US 2011/0237612 A1 · Thienylamino pyrimidines for use as Fungicides

Abstract

Thienylaminopyrimidines of the formula (I) in which to R1 to R10 and X1 and X2 have the meanings given in the description, and agrochemically active salts thereof, their use and also methods and compositions for controlling phytopathogenic harmful fungi in and/or on plants or in and/or on seed of plants, processes for preparing such compositions and treated seed and also their use for controlling phytopathogenic harmful fungi in agriculture, horticulture and forestry, in the protection of materials and in the domestic and hygiene field. The present invention furthermore relates to a process for preparing thienylaminopyrimidines of the formula (I).

A compound of formula (I)

wherein
X1 represents sulphur or CR1,
X2 represents sulphur or CR2,
where exactly one of the radicals X1 and X2 represents a sulphur atom,
R1 represents hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen,
if X2 represents CR2,
R2 and R3 independently of one another represent hydrogen, halogen, CN, nitro, OR10, O(CH2)mOR10, O[C(R10)2]mOR10, O[C(R10)2]mN(R10)2, OCOR11, SR10, SOR10, SO2R10, C═OR10, CH═NOR10, CR11═NOR10, COCl, CON(R10)2, COOR10, NR10COR10, N(R10)2, [C(R10)2]mCN, (CH2)mOR10, (CH2)mSR10, [C(R10)2]mSR10, (CH2)mSOR10, (CH2)mSO2R10, (CH2)mN(R10)2, [C(R10)2]mN(R10)2, (CH2)mCOR10, [C(R10)2]mCOR10, unsubstituted or substituted C1-C8-alkyl, C2-C6-alkenyl or C1-C8-haloalkyl;
where m=1-4,
where the substituents independently of one another are selected from the group consisting of:
hydrogen, fluorine, chlorine or bromine, C1-C4-alkyl, C1-C4-alkoxy, hydroxyl, oxo, C1-C4-haloalkyl and cyano,
where, if X2 represents a sulphur atom, the above definitions apply only to R3,
R4 represents hydrogen, C1-C4-alkyl, C1-C4-alkoxy or halogen,
R5 represents hydrogen, C1-C2-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-trialkylsilyl, C1-C4-trialkylsilylethyl, C1-C4-dialkylmonophenylsilyl, CHO, (C1-4-alkyl)carbonyl, (C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C3-C6-alkenyloxy)carbonyl, (C3-C6-cycloalkyl)carbonyl, (halo-C1-C4-alkoxy-C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, (C1-C4-alkoxy)carbonyl, (C1-C4-haloalkoxy)carbonyl, benzyloxycarbonyl, unsubstituted or substituted benzyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, C1-C2-alkylsulfinyl or C1-C2-alkylsulphonyl,
where the substituents independently of one another are selected from the group consisting of:
hydrogen, halogen, nitro, C1-C4-alkyl, C1-C4-alkoxy, hydroxyl, C1-C4-haloalkyl of and cyano,
R6 represents hydrogen, C1-C3-alkyl, cyano or C1-C3-haloalkyl,
R7 represents halogen, cyano, C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-haloalkyloxy, SMe, SOMe or SO2Me,
R8 represents hydrogen, C1-C2-alkyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C6-trialkylsilyl, C1-C4-trialkylsilylethyl, C1-C4-dialkylmonophenylsilyl, (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, (C1-C4-alkoxy)carbonyl, unsubstituted or substituted benzyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, C1-C6-alkylsulphinyl, C1-C6-alkylsulphonyl, C1-C6-haloalkylsulphinyl or C1-C6-haloalkylsulphonyl,
where the substituents independently of one another are selected from the group consisting of:
fluorine, chlorine and bromine atoms, cyano, hydroxyl, methoxy and CF3,
R9 represents straight-chain or branched unsubstituted or substituted C1-C7-alkyl, straight-chain or branched unsubstituted or substituted C2-C7-haloalkyl, unsubstituted or substituted C3-C7-cycloalkyl, straight-chain or branched unsubstituted or substituted C3-C7-cycloalkyl-C1-C3-alkyl, straight-chain or branched unsubstituted or substituted C3-C7-alkenyl, straight-chain or branched unsubstituted or substituted C3-C7-alkynyl, straight-chain or branched unsubstituted or substituted C1-C4-alkoxy-C1-C4-alkyl, straight-chain or branched unsubstituted or substituted C1-C4-haloalkoxy-C1-C4-alkyl, 2-methyl-1-(methylsulphanyl)propan-2-yl or oxetan-3-yl,
or
R8 and R9 together with the nitrogen atom to which they are attached form an unsubstituted or substituted 3- to 7-membered saturated cycle which may contain up to one further heteroatom selected from the group consisting of oxygen, sulphur and nitrogen,
R10 are identical or different and represent hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, unsubstituted or substituted C3-C6-cycloalkyl, C1-C4-trialkylsilyl, unsubstituted or substituted C2-C4-alkenyl, unsubstituted or substituted C2-C4-alkynyl, unsubstituted or substituted phenyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl, unsubstituted or substituted benzyl or a 3- to 7-membered unsubstituted or substituted saturated or unsaturated cycle which may contain no or up to four heteroatoms selected from the group consisting of N, O and S, where two oxygen atoms are not adjacent,
or,
if two radicals R10 are attached to a nitrogen atom, two radicals R10 may form a 3- to 7-membered unsubstituted or substituted saturated or unsaturated cycle which may contain up to four further heteroatoms selected from the group consisting of N, O and S, where two oxygen atoms are not adjacent,
or
if two radicals R10 are adjacent in the grouping NR10COR10, two radicals R10 may form a 3- to 7-membered unsubstituted or substituted saturated or unsaturated cycle which may contain up to four further heteroatoms selected from the group consisting of N, O and S, where two oxygen atoms are not adjacent,
R11 are identical or different and represent C1-C8-alkyl, C1-C8-haloalkyl, C1-C4-trialkylsilyl, unsubstituted or substituted C2-C6-alkenyl, unsubstituted or substituted C2-C6-alkynyl, unsubstituted or substituted C3-C6-cycloalkyl, unsubstituted or substituted aryl, C1-C4-alkoxy-C1-C4-alkyl, unsubstituted or substituted benzyl or a 3- to 7-membered unsubstituted or substituted saturated or unsaturated cycle which may contain no or up to four heteroatoms selected from the group consisting of N, O and S, where two oxygen atoms are not adjacent,
where the substituents in R10 independently of one another are selected from the group consisting of:
methyl, ethyl, isopropyl, cyclopropyl, fluorine, chlorine and bromine atoms, methoxy, ethoxy, methylmercapto, ethylmercapto, cyano, hydroxyl and CF3,
and agrochemically active salts thereof.

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Thienylamino pyrimidines for use as Fungicides

Life of this patent

Thienylamino pyrimidines for use as Fungicides

Life of this patent

Abstract

Claims21